40359-32-8

Usage

Uses

Used in Perfumery and Personal Care Industry:
3-(Allyloxy)benzaldehyde is used as a fragrance ingredient for its sweet, floral scent, contributing to the pleasant aroma of perfumes, soaps, and other personal care products.
Used in Food and Beverage Industry:
In the food and beverage industry, 3-(Allyloxy)benzaldehyde is used as a flavoring agent to enhance the taste and aroma of various products, capitalizing on its appealing flavor profile.
Used in Medical and Pharmaceutical Industry:
Due to its potential antibacterial properties, 3-(Allyloxy)benzaldehyde is considered for use in medical and pharmaceutical products, where it may contribute to the development of new treatments or applications in healthcare.
Used in Commercial and Industrial Applications:
Owing to its versatile uses and pleasant aroma, 3-(Allyloxy)benzaldehyde is widely utilized in a range of commercial and industrial applications, reflecting its broad appeal and functionality in different sectors.

InChI:InChI=1/C10H10O2/c1-2-6-12-10-5-3-4-9(7-10)8-11/h2-5,7-8H,1,6H2

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 106-95-6 allyl bromide 
• 38697-17-5 sodium salt of meta-hydroxybenzaldehyde 
• 5651-87-6 3-(propargyloxy)benzaldehyde 
• 107-18-6 allyl alcohol 
• 107-05-1 3-chloroprop-1-ene 
• 1369494-72-3 1-(allyloxy)-3-vinylbenzene 
• 1369494-77-8 (E)-1-allyloxy-3-(prop-1-en-1-yl)benzene 
• 591-20-8 3-Bromophenol 
• 66921-90-2 (E)-3-(prop-1-en-1-yl)phenol 
• 103203-83-4 3-(allyloxy)benzoic acid 
• 83230-73-3 3-allyloxy-benzoyl chloride 
• 34905-07-2 3-(2-propenyloxy)benzyl alcohol 

Downstream Products

• 79950-42-8 2-allyl-3-hydroxy-benzaldehyde 
• 79250-49-0 1-(3-(allyloxy)phenyl)ethan-1-ol 
• 100-83-4 meta-hydroxybenzaldehyde 
• 34905-07-2 3-(2-propenyloxy)benzyl alcohol 
• 861227-10-3 [1-(3-Allyloxy-phenyl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine 
• 383424-00-8 S-(3-(3-formylphenoxy)propyl) ethanethioate 
• 777079-77-3 2,4-diallyl-3-hydroxybenzaldehyde 
• 864148-10-7 (3-allyloxy-benzylidene)-(4-trifluoromethyl-benzyl)-amine 
• 864148-09-4 (3-allyloxy-benzylidene)-(4-methoxy-benzyl)-amine 
• 371754-67-5 (3-allyloxy-benzylidene)-benzyl-amine 
• 360075-38-3 (3R,4S)-1-benzoyl-3-triisopropylsilyloxy-4-(m-allyloxyphenyl)azetidin-2-one 
• 360075-34-9 C₅₁H₅₅NO₁₅ 
• 360075-42-9 C₆₆H₈₉NO₁₅Si₂ 
• 360075-41-8 C₆₈H₉₃NO₁₅Si₂ 

Relevant academic research and scientific papers

Synthesis of treprostinil: Key claisen rearrangement and catalytic pauson-khand reactions in continuous flow

A new synthesis of treprostinil is described using a plug flow reactor in two of the key steps. First, a Claisen rearrangement reaction is described in scaled flow at multigram amounts. Yields and selectivity of this step are sharply improved compared to those from previous syntheses. Second, the key Pauson-Khand reaction in flow is described under catalytic conditions with 5 mol% of cobalt carbonyl and only 3 equiv. of CO. Scaling up of this reaction safely ensures a good yield of an advanced intermediate which is transformed into treprostinil in three steps. Other improvements are the introduction of the carboxymethyl chain into the phenol from the beginning to reduce the protection-deprotection steps. The synthesis is completed in 14% global yield after 12 linear steps from (S)-epichlorhydrin.

TBuO 2H/Cu(acac) 2-Mediated Intramolecular Oxidative Lactonization of o -Allyl Arylaldehydes: Synthesis of 1-Oxoisochromans

A concise route for the tBuO 2H/Cu(acac) 2-mediated synthesis of 1-oxoisochromans is described. This includes: (i) oxidation of oxygenated o -allyl arylaldehydes and (ii) sequential intramolecular lactonization of the resulting olefin-containing benzoic acids. A plausible mechanism is proposed and discussed.

Turn on chemiluminescence-based probes for monitoring tyrosinase activity in conjunction with biological thiols

We report a chemiluminescent probe (CLPT1) that permits the paired detection of tyrosinase (Tyr) and biological thiols. Tyr only leads to a poor chemiluminescence response, a finding ascribed to the formation of a stableo-benzoquinone intermediate. The addition of glutathione (GSH), or ascorbate to theo-benzoquinone intermediate results in thiol conjugation or reduction to this intermediate, respectively. This produces a strong chemiluminescence response. Thiol co-dependence was demonstrated in live cells using the cell permeable analogue,CLPT3. The present chemiluminescence-based strategy allows the concurrent detection of tyrosinase activity and biological thiols.

PdCl2/CuCl2/Bi(OTf)3-promoted Construction of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes and Arylnaphthalenes via Intramolecular Annulation of Sulfonyl o-Allylarylchromanones

PdCl2/CuCl2/Bi(OTf)3-promoted intramolecular domino annulation of sulfonyl o-allylarylchromanones provides tetracyclic sulfonyl dibenzooxabicyclo[3.3.1]nonanes and bicyclic arylnaphthalenes with good to excellent yields in MeOH at room (25 °C) and refluxing (65 °C) temperature, respectively. The starting sulfonyl o-allylarylchromanones can be easily obtained from the intermolecular cyclocondensation of α-sulfonyl o-hydroxyacetophenones and o-allylbenzaldehydes. The uses of various catalysts and solvent systems are investigated herein for convenient transformation. A plausible mechanism is proposed and discussed. This protocol provides one-pot ring closure via carbon-carbon (C?C) bond formation. (Figure presented.).

Ancillary ligands switch the activity of Ru–NHC-based oxidation precatalysts

Herein we demonstrate how the inner-sphere coordinating ligands switch the activity of Ru–NHC-based oxidation precatalysts in the oxidative conversion of olefins to carbonyl compounds, with the help of a series of systematically varied imidazolydene-NHC (Im-NHC) and triazolydene-NHC (Tz-NHC)-based ruthenium(II)-complexes. It is shown that the catalytic activity of the para-cymene-containing precatalysts varies in the order of [(Tz-NHC)Ru(para-cymene)Cl]+ > [(Im-NHC)Ru(para-cymene)Cl]+, while the order of activity of the MeCN-containing precatalysts is found to be reversed, i.e., [(Im-NHC)Ru(MeCN)4]2+ > [(Tz-NHC)Ru(MeCN)4]2+. Along with the electronic influence of the NHC ligands, the effect of the lability of the para-cymene and MeCN ligands, and the overall charge of the complexes might be attributed toward such a switching of catalytic activity. This finding led to develop a new precatalyst with improved activity which was further utilized in selective oxidation of a series of styrene substrates containing other oxidation-sensitive functionalities.

Visible-light mediated facile dithiane deprotection under metal free conditions

Visible light mediated facile and selective dithiane deprotection under metal free conditions is developed. Eosin Y (1 mol%) proved to be an effective catalyst for the dithiane deprotection under the ambient photoredox conditions. The standard household compact fluorescent light source (CFL bulb) proved to be effective under open-air conditions in aqueous acetonitrile at room temperature. The protocol that exhibits a broad substrate scope and functional group tolerance has been shown to expand to a range of transformations for the electron-rich and -deficient thioacetals and thioketals. The synthetic utility of this protocol has also been demonstrated by gram-scale application.

Diethylaminosulfur Trifluoride (DAST)-Mediated Intramolecular Benzannulation of o-Allylchalcones: Synthesis of 3-Fluorotetralins

A concise route for the synthesis of 3-fluorotetralines is described, including: (i) NaBH 4 -mediated reduction of oxygenated o -allylchalcones and (ii) sequential DAST-mediated intramolecular annulation of the resulting alkenols. A plausible m

A molybdenum based metallomicellar catalyst for controlled and chemoselective oxidation of activated alcohols in aqueous medium

A surfactant based oxodiperoxo molybdenum complex, which could activate molecular oxygen, has been employed as a catalyst for controlled oxidation of benzylic alcohols to corresponding carbonyls. The oxidation reactions were carried out under aqueous environment, however, in the absence of any extraneous base or co-catalyst. Sensitive/oxidizable functional groups like cyano, sulfide, hydroxyl, aryl-hydroxyl, alkene (internal/terminal), alkyne (internal/terminal), and acetal were tolerated during the transformations. Such selectivity is attributed to the mild nature of the catalyst. The methodology could also be scaled-up for multi-gram synthesis and the protocol is likely to find practical use since it requires an inexpensive recyclable-catalyst and easily available oxidant (under green conditions). A plausible mechanism is proposed with the help of preliminary computational study.

Coordination Booster-Catalyst Assembly: Remote Osmium Outperforming Ruthenium in Boosting Catalytic Activity

Presented herein is a set of bimetallic and trimetallic “coordination booster-catalyst” assemblies in which the coordination complexes [RuII(terpy)2] and [OsII(terpy)2] acted as boosters for enhancement of the catalytic activity of [RuII(NHC)(para-cymene)]-based catalytic site. The boosters accelerated the oxidative loss of para-cymene from the catalytic site to generate the active catalyst during the oxidation of alkenes and alkynes into corresponding aldehydes, ketones and diketones. It was found that the boosting efficiency of the [OsII(terpy)2] units was considerably higher than its congener [RuII(terpy)2] unit in these assemblies. Mechanistic studies were conducted to understand this unique improvement.

Synthesis of 3-Azidopiperidine Skeleton Employing Ceric Ammonium Nitrate (CAN)-Mediated Regioselective Azidoalkoxylation of Enol Ether: Total Synthesis of D2 Receptor Agonist (±)-Quinagolide

The total synthesis of (±)-quinagolide, which is a D2 receptor agonist, was accomplished via a ceric ammonium nitrate (CAN)-mediated regioselective azidoalkoxylation of enol ether route. Key features of the synthesis include Claisen rearrangement, PPTS (pyridinium p-toluenesulfonate)-catalyzed one-pot acetal deprotection, followed by a diastereoselective Henry reaction, which enables construction of the required trans ring junction and CAN-mediated regioselective azidoalkoxylation of enol ether. The PPTS-catalyzed intramolecular diastereoselective Henry reaction to fix three contiguous stereocenters on tetrahydronaphthalene and the first-of-its-kind synthesis of the 3-azidopiperidine skeleton, using a CAN-mediated regioselective azidoalkoxylation of enol ether, are important findings of the present work.